Sometimes callers tell you the most ridiculous stories about things they’ve done. Sometimes they were caught by others, other times they were not. One caller told me about how in his youth he really liked to be outdoors naked. Now that doesn’t seem too odd, and I suppose if you’re lucky enough to live in the country and have a good bit of land with no one around, you could indeed wander around nude and no one would see. Alas this caller was not in the country and it was wintertime, and thirty degrees when the mood struck him.
He decided to remove his clothes and have a quick jog around the immediate area where he was. Not around the block, but through a few backyards. A neighbor saw him, but since he was running, she didn’t see his face, only a naked man running in the snow. She called the other neighbors telling them to be on the lookout for a naked man running around the neighborhood. He had his odd fun, quickly put his clothes back on and went back home before someone grabbed him. He came in and his mom asked him if he’d happened to see a naked man running around outside.
He said it was all he could do not to laugh, since of course he’d been the naked man the ladies in the neighborhood were all in a tizzy about, but they did not know that. So she actually told him to go back out and have a look around the neighbors yards, to see if he could find this fiendish, wintertime streaker. He was laughing as he was relating this ridiculous story from his youth. Many people do enjoy being nude outdoors, but in the snow? That’s a bit cold, to be sure. It was a lot of fun for him and gave him a fairly harmless wintertime memory.
It’s not uncommon to find men that wish to be kept in chastity. One frequent caller told me he wishes I could be the keyholder for his chastity device. He said he’s been training himself to cum via dildos up his ass and he wishes a real man would fuck him. He’s a virgin of nearly thirty years of age with zero confidence. He would like to watch a woman get fucked in front of him and then have the man fuck him, while his penis is contained in a cock cage, so he’s unable to masturbate. He said he’s been able to make himself cum with the dildos, he can only image what getting fucked by a real cock would be like.
I suggested he try a butt plug, for an even more full sensation than the dildo provides. Some have revealed they wear butt plugs for hours and hours on end. One can only wonder if they are stretching themselves and may in the future need adult diapers due to this, dreadful thought that is. Oh well, it’s their own backside to destroy as they wish, consequences be damned. One even called me while he was driving and claimed to have a butt plug in while he was and he claimed it had been in for six hours. No idea what the average length of time is for one to wear one, but six hours seems a long time!
Cock cages are more popular than one would imagine. Ones asking for keyholders are also pretty common. Some online programs let strangers access the locking mechanism and it’s all done remotely, they don’t need to actually mail you a key to keep their junk locked up. What will they think of next? I think random locking would be funny, where they were wearing them and thought they could get out at any time, only to have someone else actually be in control of it.
Every fall there’s a yard clean up that happens. Saplings get cut down that have taken root, leaves get raked, the man that mows the lawn does these yearly chores as well. He’s a handsome young guy. His father used to do it, but he’s getting older now, so the son does most of the work. I’ve watched him grow up, coming over to help when he was young, and now he’s a man. I invited him in the afternoon of the crisp, fall day he came. He’d worked for several hours and I had some hot cider on the stove.
He came inside and he didn’t realize the cider was hard. He started to feel quite relaxed. I told him I’d always liked him and he’d grown into a handsome young man. I told him I found him quite attractive, and wondered if he might feel the same about me? He looked a bit shy and embarrassed, but I could see his cock getting hard in his pants. I boldly reached down and gave it a light squeeze. He didn’t stop me. I unzipped him and reached my hand inside and began stroking him. I then got extra bold and led him by the cock to my bedroom.
I undressed him and laid him on his back on the bed and quickly disrobed myself. I quickly got on the bed and straddled him, sinking down onto his erect cock and I began to rock back and forth on top of him. He rubbed my nipples as I fucked him, and he made very sexy sounds that turned me on. I made myself cum easily on his young shaft before he finally squirted into me. Fall always was my favorite time of year. I look forward to him coming around again in a bit when it’s time to begin snow shoveling.
It goes without saying that man callers are shy men that have no luck with women in their own lives. Phone sex is it for them, masturbation and talking to a lady is as much intimacy as some will ever know. Some come right out and confess they are shy and don’t get any girls, that a Fleshlight or pocket pussy is the closest they have ever come. Some might have a small penis, others are average sized, but simply lacking in the much needed confidence they need. I asked one such shy caller what he would do if an aggressive woman came onto him if she found him attractive. He said he’d be very uncomfortable.
It’s surprising how many callers have related such things. One caller that was a virgin until he was in his mid thirties used to say after he finally did get a girlfriend, many times he’d pretend to be asleep since her sexual demands would intimidate him. It’s mind boggling that some men can be like this. One caller that’s a long term one is a nice man, he seems very nice, just too shy to get a real woman, although he’s divorced. Likely because he was so shy. I call him the timid pervert, although he’s quite tame. He doesn’t even like to talk about sex during calls, he just calls for permission to masturbate.
There’s never any talk of blow jobs, or fucking, he just wants me to tell him it’s ok for him to hump his pillow. He told me he liked a lady a few years ago, and he thought she’d be open to a sexual encounter, but he said he just didn’t have the confidence to seal the deal, so he went home alone as always. It’s kind of sad, but people are many times their own worst enemies.
Never underestimate a horny female. Many do. They don’t realize girls can be even more creative in their masturbation playing than guys can be. One of the rare times a woman called and told me some of the odd ways she’s masturbated and she said when she was younger and came home from school and had the house to herself she used to rub her pussy against the corner of the kitchen table. I’d never heard of that before.
The closest thing I ever tried was the bed I used to have had a foot board and one of the decorative corners of it was about at crotch level and I tried grinding on it, but it was a bit hard to keep my balance on one foot and I wasn’t able to get to orgasm trying it. I always thought of that time I did so though every time I looked at the post! I never tried rubbing on a doll or anything, but many girls do that, some even insert Barbie dolls, that could go very wrong, and is not advised. Horny people often are not thinking clearly though and not thinking what could happen if things go wrong.
She told me how she’d take her skirt or pants off when she came in and realized she was alone for a while, and she was always afraid someone would come in and catch her. The chances would be high for a high traffic room like a kitchen someone could come home and walk in and she’d be bucking against the corner of the table, getting the corner of it slick with her cunt juice as she tried to get her self off. For many young girls, masturbation is a huge part of their lives, just like it is with guys, before bed, in the shower, after school, there’s no end to the self pleasuring when you’re young and horny.